Oxygenated indan compounds and method of making the same



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OXYGENATED INDAN COMPOUNDS AND METHOD OF G THE SAME No Drawing. Application February 4, 1954 Serial No. 408,298

6 Claims. (Cl. 260-490) The present invention relates to novel chemical compounds and to the method of preparing the same; and, more particularly, the invention relates to oxygenated indan compounds possessing therapeutic, particularly bypotensive properties.

Many agents are known to produce a lowering of the blood pressure in a living body. Unfortunately, most of these substances possess such limitations and disadvantages as to render them practically unusable as specific therapeutic agents in the treatment and relief of hypertension. Thus, in many cases the hypotensive effect of these agents is only transitory, while others produce undesirable side effects on the system even at levels that are only partially effective hypotensively. Many of the agents cannot be administered orally since they have an irritating or corrosive efiect on the stomach or intestinal wall, and even when administered parenterally, the results as far as relief from hypertension is concerned are erratic.

It is the principal object of the present invention to provide compounds possessing valuable hypotensive properties.

It is another object of the invention to provide compounds possessing hypotensive properties which may be administered at therapeutic levels orally as well as par: enterally.

Other objects, including the provision of a novel method of making the compounds, will become apparent from a consideration of the following specification and the claims.

The compounds of the present invention are oxygenated indan compounds comprising the fundamental structural formula:

where R is selected from the group consisting of aminoalkoxy, monoalkylaminoalkoxy, dialkylaminoalkoxy, dialkylaminoalkoxyalkyl and N-alkylpiperidyloxy groups, the alkyl and alkoxy groups of which contain from 1 to 4 carbon atoms; where R is selected from the group consisting of hydrogen, halogen, phenyl and alkyl groups containing from 1 to 4 carbon atoms; where R is selected from the group consisting of hydrogen, hydroxy, alkyl and alkoxy groups containing from 1 to 4 carbon atoms, and where X is selected from the group consisting of where R, is an alkyl group containing from 1 to 4 carbon atoms.

or ice 2,820,817 l ate nted Jan. 1958 OXY group j E N-R From the standpoint of optimum hypotensive activity, the compounds wherein R is a dialkylaminoalkoxy group are preferred. The R groups set forth above will contain from 1 to 4 carbon atoms and may be methyl, ethyl, npropyl, isopropyl, n-butyl, sec-butyl or tert-butyl groups. The term'Alk in the foregoing discussions refers to alkylene group containing from 1 to 4 carbon atoms, such as methylene, ethylene, trimethylene, propylene, and the like. In the compounds which are preferred from the standpoint of optimum hypotensive activity the R group is located at the six position on the molecule.

R may be, as stated above, hydrogen, a halogen, such as chlorine, bromine, and the like, phenyl or an alkyl group containing from 1 to 4 carbon atoms such as those mentioned above in connection with R In the preferred compounds of the invention, R is either hydrogen or an alkyl group, particularly a methyl group. The exact position of R, on the molecule is not critical from the standpoint of the broader aspects of the invention, although it is preferably located at the two position.

R may be hydrogen or an alkyl group containing from 1 to 4 carbon atoms such as those mentioned above in connection with R R may also be an alkoxy group containing from 1 to 4 carbon atoms such as methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, sec-butoxy and tert-butoxy. In the preferred compounds R is hydrogen. The position of R on the molecule may also vary from any of the positions in accordance with the broader aspects of the invention. However, in the preferred compounds, R is located at the five position.

X may be varied somewhat to provide nuclei varying from the indan nucleus, where X is CH to, when Xis 0 II c and the other groups mentioned above, the indanone nucleus and derivatives thereof. In connection with the latter, X may be in which latter two cases, R is an alkyl group containing from 1 to 4 carbon atoms such as those mentioned above in connection with R In the preferred compounds In the compounds of the invention one equivalent of acid may be added to the nitrogen of the R group to form a salt. Hence, the compounds of the invention may be prepared and/or employed either as the base or as a salt. In view .of the fact that the salts differ from the bases only in the addition of the acid to the stated nitrogen atom and are;characterize'd by the same fundamental, structural formula, the salts as well as the bases are included Within the scope of this specification and of the claims where reference is made to a compound comprising the stated fundamental structure.

The acid forming the salt may be any inorganic or organic acid desired, for example, hydrochloric, hydro- I bromic, hydriodic, nitric, sulfuric, phosphoric, and the like; acetic,- propionic, caproic, stearic, and other acids of thisseries, and the like; crotonic, fumaric, oleic, oxalic, citric, tartaric, lactic, benz oic, naphthoic, picric, salicylic, dilituric, methane sulfonic, camphor sulfonic, and the like. If a salt is to be administered, any toxicity of other undesirable properties which may be imparted by the acid should be taken into consideration as well known in the art. a

It will be seen from the foregoing that the compounds possessing optimum hypotensive properties and which are, therefore, thepreferred compounds of the invention are those comprising the fundamental structural formula:

and

--C-H- where R, is an alkyl group consisting" of from 1 to 4 carbon atoms, particularly The compounds may be readily prepared-by condensing one mol of an appropriate hydroxy indan or indan derivative providing the desired X, R (except halogen) and R groups, with one mol of the appropriate am'injo-, alkyl substituted amino-, or alkyl substituted amino-alkyl halide or N-alkylpiperidyl halide providing the desired R group. The reaction may be conducted in an aqueous or nonaqueous medium, such as a mixture of Water and methanol or an anhydrous mixture of methyl alcohol and benzene, in the presence of a'base, such as sodium hydroxide, sodium methoxide, potassium ethoxide, and the like. The temperature conditions may vary widely; however, it is preferable to employ an elevated temperature at or near the boiling point in order to hasten the reaction. In this connection, carrying out the reaction under refiuxat atmospheric conditions is particularly advantageous, and under these conditions the reaction is completed in from one to a few hours. W

In recovering the product, off or the compound precipitated as a salt by the addition of an acid, such as hydrogen chloride, to the mixture. When the reaction medium isa'ttiixture of methyl alcohol and benzene it is desirable to add water to the mixture recovering the product from the benzene layer. The product, if in the form of the base, may be purified by distillingeither under vacuum or atmospheric conditions.-

the solvent may be distilled 4 If the product is recovered in salt form it may bepurified by recrystallization from, for example, methyl ethyl ketone or a mixture of ether and methyl alcohol.

The foregoing reactions are suitable in the situations where R is other than halogen. Where R in the final compound is to be halogen, the halogen is added to the compound prepared as described above as by reacting the compound with the desired halogen in non-aqueous medium, such as an anhydrous mixture of methanol and ether.

An alternative procedure for preparing compounds in which X is involves reduction of the corresponding indanone as by hydrogenation under pressure in the presence of a palladium carbon catalyst; Likewise, the products in the form of the indanol can be readily converted into the corresponding indanyl esters by reaction with the appropriate acid halides. I

The hydroxy'indan or indan derivatives for the mostpart for use in the above-described reactions may readily be prepared by demethylation of the corresponding methoxy derivative as by refluxing the methoxy derivative in benzene in the presence of aluminum bromide. In the case where R, in the final compound is to be an alkoxy group, the hydroxy indanone compound maybe prepared by cyclization of the corresponding acid, fol lowed by reduction to the corresponding indanol or indan.

The compounds of the present invention and their preparation may be better understood from a consideration of the following examples which are given for the purpose of illustration only and are not to be considered as limiting the scope of the invention in any way.

Example I A mixture of 6 g. of 6 -methoxy-l-indan'one, 32 g. of aluminum bromide and 200 ml. of dry thiophene-free benzene is refluxed for four and one-half hours. The resulting mixture is cooled and decomposed with ice and hydrochloric acid. The benzene layer is separated and the acid layer extracted with ether. The extracts are combnied and dried over anhydrous sodium sulfate. The ether is removed under vacuum, and the crude product recrystallized from ethanol. The resulting 6-hydroxy-1- indanone melts at 15l-l53 C.

To a solution of sodium methoxide prepared from 0.3 g. of sodium and 25 ml. of methanol is added 1.48 g. (0.01 mol) of 6-hydroxy-l-indanone and 1.36 g. (0.01 mol) of diethylaminoethyl chloride, and the mixture is refluxed for one and one' half hours. The methanol is removed under vacuum, water is added, and the resulting mixture is extracted with ether. After drying a short period over anhydrous potassium carbonate, the ether is removed and the product further dried in a vacuum oven. The product is then dissolved in ml. of dry ether andhy'drogen chloride is introduced. The resulting h y drochloride is removed by filtration and recrystallized from a mixture of methanol and ether. The resulting 6- (2diethylaminoethoxy)-l-indanone hydrochloride melts at 183-184 C. The calculated N content for is 4.9; that found was 4.9.

8 milligrams of the product per kilogram of body weight reduces the blood pressure substantially.

Example [I Following the procedure of Example I, using, however, 3 g. (0.03 mol) of crude S-dimethylaminoethyl chloride in place of the diethylaminoethyl chloride results in 6-(Z-dimethylaminoethoxy)" l' indanone hydrochloride melting at 210-211" C. The calculated N content for C H ClNO is 5.5; that found is 5.4. I

Following the same procedure butusing -B-d ipropyl aminoethyl chloride, B-diisopropylaminoethyl chloride, 18- dibutylaminoethylchloride and fl-diisobutylaminoethyl chloride in place of dimethylaminoethyl chloride, the corresponding 6-(B-dipropylaminoethoxy)-1-indanone, 6-(,8- diisopropylaminoethoxy)-1-indanone, 6-(fi-dibutylaminoethoxy)-l-indanone and 6-(B-diisobutylaminoethoxy)-1- indanone respectively are prepared.

Example III Example IV Following the procedure of Example I, using, however, 1.3 g. of 6-hydroxy-2-methyl-l-indanone and 1 g. fi-dimethylaminoethyl chloride results in 6-(2-dimethylaminoethoxy)-2-methyl-l-indanone hydrochloride melting at 200-202 C. The calculated N content for C H ClNo is 5.2; that found is 5.1.

Only 4 milligrams of this compound per kilogram of body weight reduces the blood pressure substantially.

Example V To a solution of sodium methoxide prepared from 1.2 g. (0.05 mol) sodium and 50 ml. methanol is added 8.1 g. (0.05 mol) of 6-hydroxy-2-rnethyl-l-indanone and 7.4 g. (0.05 mol) of 3-chloro-l-ethylpiperidine. After refluxing for six hours, the mixture is cooled and the precipitated sodium chloride removed by filtration. The filtrate is concentrated under vacuum and diluted with water. The aqueous mixture is extracted with ether and the combined extracts dried over anhydrous sodium sulfate. Passage of hydrogen chloride into an ether solution of the product followed by recrystallizations from a mixture of methanol and ether gives l-ethyl-3-(1-oxo-2-methyl-6- indanoxy) piperidine hydrochloride melting at 199-201 C. The calculated N content for C H ClNO is 4.5; that found is 46:0.1.

4 milligrams of the compound per kilogram of body weight reduces the blood pressure significantly.

Example VI Following the procedure of Example V using, however, 3 g. of 6-hydroxy-1-indanone and 3.2 g. of 3-chloro-1- ethylpiperidine and a mixture of acetone, methanol and other during the recrystallizations results in 1-ethyl-3-(1- oxo-o-indanoxy) piperidine hydrochloride melting at 198200 C. The calculated N content for C H ClNO is 4.7; that found is 4.5.

About 8 milligrams of the compound per kilogram of body weight reduces the blood pressure significantly.

By using 6-hydroxy-2-ethyl-l-indanone, 6-hydroxy-2- propyl-l-indanone, G-hydroxy-Z-isopropyl-l-indanone, 6- hydroxy-Z-butyl-l-indanone and 6-hydroxy-2-isobutyl-lindanone in place of 6-hydroxy-l-indanone there results 1-ethyl-3-(l-oxo-2-ethyl-6-indanoxy) piperidine, l-ethyl-3- (1-oxo-2-propyl-6-indanoxy) piperidine, 1-ethyl-3-(1-oxo- 2-isopropyl-6-indanoxy) piperidine, lethyl-3-(l-oxo-2- butyl-6-indanoxy) piperidine and 1-ethyl-3-(l-oxo-2-isobutyl-6-indanoxy) piperidine, respectively.

Example VII A solution of 7 g. (0.026 mol) of 6-(p-dimethylaminoethoxy)-2-methyl-l-indanone hydrochloride of Example IV in 100 ml. of water is subjected to hydrogenation at 58.8 p. s. i. in the presence of palladium-carbon catalyst. Reduction is allowed to take place over a period of 18 solvent removed by evaporation under vacuum. The residue is recrystallized from methyl ethyl ketone containing a few drops of methanol to provide o-(p-dimethylaminoethoxy) -2-methyl-1-indanol hydrochloride melting at 136-137" C. The calculated N content for C H ClNO is 5.2; that found is 5.1.

In a similar manner using, however, the indanones described in Examples 1, II, III, V, VI, IX, XI, XII, XIII, XIV, XV, XVI, XVII, XX and XXII in place of 6-(B-dimethylaminoethoxy)-2-methyl-l-indanone, the corresponding 6-(2-diethylaminoethoxy)-l-indanol, 6-(2-dimethylaminoethoxy) 1 indanol, 6-(2-diethylaminoethoxy) 2-methyl-1-indanol 1-ethyl-3-( l-hydroxy-Z-methyl-G- indanoxy) piperidine, l-ethyl-3-( l-hydroxy-o-indanoxy) piperidine, 6-(Z-dimethylaminoethoxy)-2-ethyl-1-indanol, 2 bromo 6 (2 dimethylaminoethoxy) l indanol, 6- (2 diethylaminoethoxy) 5 methoxy 1 indanol, 5-(2- dimethylaminoethoxy 1 indanol, 6 (2 dimethylaminoisopropoxy) 2 methyl 1 indanol, 7 (2 diethylaminoethoxy) 4 methyl 1 indanol, 6 (2 diethylaminoethoxy) 2 phenyl -'1 indanol, 6 (2 ethylaminoethoxy) 2 methyl 1 indanol, 6 (2 aminoethoxy) 2 methyl 1 indanol, 5 (2 diethylaminoethoxy) 4 hydroxy l indanol are prepared.

8 milligrams of the compound per kilogram of body weight reduces the blood pressure substantially.

Example VIII A solution of 2.5 g. (0.01 mol) of crude 6-(fi-dimethylaminoethoxy)-2-methyl-1-indanol in 50 ml. of dry benzene is treated with 1.3 g. of isobutyryl chloride, and the resulting solution is refluxed in a Water bath for one and onehalf hours. The precipitate is removed by filtration and recrystallized from methyl ethyl ketone providing 6-(fi-dimethylaminoethoxy) 2 methyl 1 indanyl isobutyrate hydrochloride melting at l74175 C. The calculated N content for C H ClNO is 4.1; that found is 4.2.

2 milligrams of this compound per kilogram of body weight reduces the blood pressure substantially.

By using acetyl chloride, propionyl chloride and butyryl chloride in place of isobutyryl chloride, the corresponding 6 (B dimethylaminoethoxy) 2 methyl 1 indanyl acetate, 6 (B dimethylaminoethoxy) 2 methyl 1 indanyl propionate and 6 (B dimethylaminoethoxy) Z-methyl-l-indanyl butyrate are prepared.

Example IX Following the procedure of Example I, using, however, 2 ethyl 6 hydroxy 1 indanone and B dimethylaminoethyl chloride, 6 (13 dimethylaminoethoxy) 2 ethyll-indanone is produced. The product is dissolved in ether and treated with hydrogen chloride. The resulting precipitate is removed by filtration and recrystallized from methyl ethyl ketone to provide 6 (,8 dimethylaminoethoxy)-Z-ethyl-l-indanone hydrochloride melting at 169- 170 C. The calculated N content for C H ClNO is 4.9; that found is 5.0.

In the same manner by replacing 2-ethyl-6-hydroxy-1 indanone with 2-propyl-6-hydroxy-l-indanone, 2-isopropyl- 6-hydroxy-l-indanone, 2-butyl-6-hydroxy-1-indauone and 2-isobutyl-6-hydroxy-l-indanone, the corresponding 6-(fldimethylaminoethoxy) 2 propyl 1 indanone, 6 (B dimethylaminoethoxy) 2 isopropyl l -indanone, 6 8- dimethylaminoethoxy) 2 butyl l indanone and 6 (fldimethylaminoethoxy) 2 isobutyl 1 indanone, respectively, are prepared.

Example X Following the procedure of Example I using Z-methyl-S- indanol and B-dimethylaminoethyl chloride provides S-(pdimethylaminoethoxy)-2-methylindan. The product is dissolved in ether and treated with hydrogenchloride. The resulting precipitate is removed by filtration and rehours. The catalyst is removed by filtration. and the M'Y li from methylfithyl ketone to PF 1(fi- 7 insomn ac-satiety) -;2fiiethylindaii hydrochloride inciting at l58 l59 C; The calculated N content for CnHnC-lNO is 5.5; that found is 5.3. v V

8 milligrams of this compound per kilogram of body weight reduces the blood pressure substantially.

In the same manner using, however, 2-propyl-5-indanol; 2-isopropyl-5-indanol, 2-butyl-5-indanol and 2-sec-butyl- Sdndauol in place of Z-methyl-S-indahol, the correspondirig -(fi-dimethylaminoethoxy)-2-propylindan, 5-(,E3-di methylaminoethoxy) 2 isopropylindan,. 5-(fl-dirnethyl aniinoethoxfl 2 butylindan and 5- (B-dimethylaminoethoxyj 2-sec-butylindan are prepared.-

' Exafnple XI To a solution of 4.7 g. of 6-(B-dirnethylaminoethoxy)- 1"- indanone in 200 ml. of ether and 200 ml. of ethanol is added withstirring 1.5 ml. of bromine. The mixture is stirred for an additional two hours and then allowed to stand overnight at room temperature. The solvent is removed by evaporation and the residue recrystallized from methyl ethyl ketone containing a few drops of methanol to provide 2 bromo 6 (,8 dimethylarninoethoxyyl indanone hydrobromide melting at l75=l77 C. The calculated N content for C l-l Br NO is 3.7; that found is 3.8.

1 milligram of this compound per kilogram of body weight reduces the blood pressure substantially.

Example XII A solution containing 17.8 (0.1 mol) of 6-hydroxy-5- nieth-oxy-l-indanone, 19 g. of diethylaminoethyl chloride hydrochloride, 9 g. of sodium hydroxide, 150 m1. of methanol and 100 ml. of water is refluxed for 66 hours. The methanol is distilled under vacuum, and the residue is extracted with ether. Evaporation of the ether and distillation of the residue gives 6-(;3-dietl1ylaminoethoxy) 5-methoxy l-indan'one, B. Ppl8l C./0.55 mm. The calculated N content for C H NO is 5.1; that found is 5.1.

The hydrochloride of the compound is prepared by passing hydrogen chloride intoan ether solution thereof and recrystallizing from methyl ethyl ketone containing a small amount of methanol. The resulting compound 6 1 (fl-fiifithylaminoethoxy)-5methoxy-l-indanone hydro chloride, melts at l72l73 C. The calculated N content for C H ClNO is 4.5; that found is 4.5.

2-4 milligrams of this compound per kilogram of body weight reduces the blood pressure substantially.

, Example XIII Following the procedure of Example I using 13.8 g. of S-hydroXy-LindanOne in place of the 6 hydroxy-1- indan'one, results in 5-(B-dimethylaminoethoxy)-l-indanone' hydrochloride melting at 2lO-2l2 C. The calculated N content for C H ClNO is 5.5 that found is 5.5,

4-16 milligrams of this compound per kilogram of body weight reduces the blood pressure substantially.

Example XIV Following the procedure of Example Xil using 6- lfq' di-oxy-2'-methyl-l-indanonev and ,e-dimethylaminoiso propyl chloride hydrochloride, -(p-dimethyl-aminoisopropoxy)-2 methyl-1-indanone is produced. The product isdissolved in ether and treated with hydrogen chloride. The resulting precipitate is removed by filtration and recrystallized from a mixture of methanol and methyl ethyl ketone to provide 6-(fi-dimethylaminoisopropoxy)- Z-methyl-l-indanone hydrochloride melting at 208-2l0 Q. The calculated N content for C I-1 G140; is 4.9; that found is 5.1. H

8 milligrams of this compound per kilogram of body weight lowers the blood pressure substantially.

7 Likewise, using B-dimethylarninopropyl chloride, B dirnethylaminobutyl chloride and B-dinietliylaniinoisobutyl chloride, in place of p-dirnetliylaifiifioisopio'pyl chloride,

indanone in place of 7-hydroxy-4-methyl-l-indanone, the

corresponding 4 (,8 dimethylaininoethoxy)-7-methyl-1 indanone is prepared.

Example X'Vr Following the procedure of Example I using, however, 6-hydroxy-2-phenyl-l-indanone and B-diethylaminoethyl chloride results in G-(fl diethylaminoethQXy)-2-pheiiyl-1- indanone boiling at 215-217" C./0.1 mm. The calculated N content for C H 5NO is 4.3; that found is 4.3.

Example X VII A solution of 7.4 g. of potassium hydroxide in 100 m1. of methanol is added gradually to a solution of 22 g. of

6-hydroxy 2-methyl-l indanone in 101 g. of ethylene.

bromide at reflux temperature. The mixture is refluxed five hours, cooled, diluted with water and extracted with chloroform. The chloroform extract is Washed with 5 percent sodium hydroxide and water respectively. Evaporation of the solvent and distillation of the residue gives 6 (-bromoethoxy)-2=rnethyl-1-indanone, B. P. 140-142? C./ 0.2 mIItL, M. P. 71'-72 C. The calculated C, H and Br content for C H' BrO is 53.6, 4.9 and 29.7 respec- 'tiv'ely; that found is 53.7, 4.9 and 29.9.

A solution of 13.5 g. of 6-(B-bromoethoxy)-2-methylbindanone and 60 cc. of percent aqueous ethyl amine in cc. of methanol is heated at 100-125 for 19 hours. The solvent is distilled under vacuum, 10 percent sodium hydroxide is added, and the resulting mixture is extracted with ether. The ether solution is extracted with dilute hydrochloric acid; The hydrochloric acid solution is neutralized with solid potassium carbonate and extracted With ether; Evaporation of the ether and distillation of the residue gives 6-(,8-ethylaminoethoxy)-2 methyl-l-indanone, B. P. l 50 C./0.47 mm. The calculated N content for C H NO is 6.0; that found is 6.2.

The hydrochloride of the compound is prepared by passing hydrogen chloride into an ether solution thereof and recrystallization from a mixture of methanol and methyl ethyl ketone, M. P. 217.5-219 C. The calcu-'- lated N content for C H ClNO is 5.2; that found is 5:4.

2-'8 milligrams of this compound per kilogram of body weight reduces the blood pressure substantially.

Following the same procedure but using methyl amine, propyl amine, isopropyl amine, butyl amine and sec-butyl amine in place of ethyl amine, the correspondin g'6-(5- methylaminoethoxy) 2-rnethyl=l indanone, 6-(B-propylaniinoethoxy) -'2-methyl-1-indanone, fi-(fi-isopropyla'minc ethoxy) '-2=methyl-l-indanoue, 6-(fi-butylarninoethoxy'y2- methyl-l-indanone and 6'-(fi-sec-butylaminoethoxy)-2 methyl-l-indanone are prepared.

Example XVIII is 5.7; that foundis 5:6.

chloride provides 7-(5-diethylaminoethoxy)-4- 1-2 milligrams of this compound per kilogram of body Example XIX A mixture of 13.5 g. of -(fi-bromoethoxy) -2-methyl-lindanone, 9.3 g. of potassium phthalimide and 200 cc. of n-butyl alcohol is refluxed 18 hours. The solution is cooled and the precipitated solid removed by filtration. Recrystallization from methyl alcohol gives N-[2- Z-methyll-oxo-6-indanoxy) ethyl] -phthalimide, melting at l49l50 C. The calculated N content is 4.2; that found is 4.1.

To a suspension of 11 g. of N-[2-(2-methyl-1-oxo-6- indanoxy)ethyll-phthalimide in 150 cc. of methyl alcohol is added 1.7 g. of hydrazine hydrate. The mixture is heated on a water bath for /2 hour, cooled and treated with 20 cc. of concentrated hydrochloric acid. The resulting mixture is heated on a water bath for 15 minutes, cooled and filtered. The filtrate is concentrated under vacuum, neutralized with 10 percent sodium hydroxide and extracted with ether. After drying the ether solution with anhydrous potassium carbonate, an ether solution of maleic acid is added. The precipitated solid is removed by filtration and recrystallized from methyl ethyl ketone. The resulting 6-(fi-aminoethoxy)- Z-methyl-l-indanone maleate melts at l57-158 C. The calculated N content is 4.4; that found is 4.3.

Following the same procedure but using S-(fi-bromoethoxy) -l-indanone, 7-( 3-bromoethoxy) lindanone, 6-( 3 bromopropoxy)-1-indanone and 6-(/3-bromobutoxy)-lindanone in place of 6-(fi-bromoethoxy)-2-methyl-1- indanone, the corresponding -(fi-aminoethoxy)-l-indanone, 7-(fi-aminoethoxy)-1-indanone, 6 (fit aminopropoxy)-1-indanone and 6-(B-aminobutoxy)-l-indanone are prepared.

Example XX Following the procedure outlined in Example XVIII using, however, 1-chloro-6-(B-dimethylaminoethoxy)-2- methylindan in place of l-chlorindan and a solution of sodium ethoxide in ethanol instead of B-diethylaminoethanol, 6-(fi-dimethylaminoethoxy)-1-ethoxy-2-methylindan is prepared.

In a similar manner using, however, a solution of sodium methoxide in methanol, sodium propoxide in propanol, sodium isopropoxide in isopropanol, sodium butoxide in butanol and sodium sec-butoxide in secbutanol, the corresponding 6-(fi-dimethylaminoethoxy)-lmethoxy-Z-methylindan, 6-(fi-dimethylaminoethoxy)-1- propoxy-Z-methylindan, 6-(fl-dimethylaminoethoxy)-1- isopropoxy-Z-methylindan, 6-(j8-dimethylaminoethoxy)-lbutoxy-Z-methylindan and 6-(B-dimethylaminoethoxy)-1- sec-butoxy-Z-methylindan are prepared.

Example XXI Following the procedure outlined in Example 701 using, however, 4,5-dihydroxy-1-indanone in place of 6-hydroxy- S-methoxy-l-indanone, the corresponding S-(B-diethylaminoethoxy)-4-hydroxy-1-indanone is prepared.

10 I claim: 1. Oxygenated indan compounds having the fundamental structural formula:

where R is an alkyl group containing from 1 to 4 carbon atoms.

2. Oxygenated indan compounds having the fundamental structural formula:

3. Oxygenated indan compounds having the fundamental structural formula:

O= 0CH:CHrN(CHa)2 4. oxygenated indan compounds having the fundamental structural formula:

0 OOH2CH2N(C1HB):

5. Oxygenated indan compounds having the fundamental structural formula:

HO O-CH2CH:N(CH:):

6. Oxygenated indan compounds having the fundamental structural formula:

CsHIGOO OCH:CHQN(CH:):

References Cited in the file of this patent Protiva et al.: Chem. Abst. (1952), vol. 46, page 8082. 

1. OXYGENATED INDAN COMPOUNDS HAVING THE FUNDAMENTAL STRUCTURAL FORMUAL:
 6. OXYGENATED INDAN COMPOUNDS HAVING THE FUNDAMENTAL STRUCTURAL FORMULA: 